The Art and Science of Cold-Emailing

Madison Gary
10 min readDec 21, 2020

This post is part of the personal sales and marketing crash course project I am undertaking in December. If you’re interested in reading about the goals I set or what I accomplished at the end of the month, feel free to click around!

Photo by Solen Feyissa on Unsplash

Cold-emailing is both a science and an art. Every good salesperson knows there is a strategic method to getting the highest open rates, but an email without personalization is like a bad pickup line.

More than two-thirds of incoming messages are promotional.

Gmail categorizes about 68 percent of incoming messages as “promotions.” Similarly, 22 percent of messages fall into the update category. That leaves about 10 percent of incoming messages that offer something of substance.

The read rate for promotional emails is 19.2%.

Even if your email lands in the Promotions tab, the game isn’t over. Many Gmail users still pick through the overflowing folder of hungry salespeople trying to get them to purchase something, but the ultimate goal is to land in the inbox of your prospect.

Doing this ensures a much higher chance of them opening and engaging in a conversation, further driving the sales pipeline.

How to get the prospect to open (and read) a cold-email

01 | Avoid Spam Trigger Words

Words like cash, bonus, sale, and make money can all trigger the spam police. An email sentenced to a lifetime in the spam folder is an email that will never get opened.

02 | Avoid formatting that could get flagged.

Having too many explication points, non-emoji symbols (@ and #), multi-colored fonts, or varying font size and type are red flags to Gmail’s spam police. Overuse of punctuation is also a major trigger for spam. Spam filters are getting tighter, especially in Gmail.

03 | Keep your subject lines engaging and straightforward.

Avoiding spam trigger words and characters that would catch a robot’s attention is only half the battle. Subject lines should include an intriguing hook and evoke curiosity that leads to a high open-rate.

The subject line is the pickup line of a dating life. No one wants a pickup line that immediately makes them cringe, and email users aren’t going to open an email that doesn’t catch their attention.

Subject lines should also be concise. Scripting the subject lines as click-bait isn’t the move. Untruthful subject lines can destroy trust between the buyer and seller, making it almost impossible to regain within the first stages of the sales cycle.

It’s best to be representative and transparent upfront so that when the prospect opens the email, they don’t feel betrayed by a misleading subject line. Subject lines should align with the brand personality.

47% of emails are opened or discarded based solely on their subject line.

Photo by Litmus

Having deceptive, misleading subject lines won’t do you any favors. High open rates and low click rates have never been the recipe for selling.

Your prospect opens the email. Now what?

The hardest part is behind you — getting the initial open. Now that the prospect has clicked on the email, how will you know if they stayed long enough to read it?

If a lead follows through with the included call to action, that’s a strong measurement that the email did what it was supposed to do.

If followed, these next points ensure a high volume of clicks and further engagement with the sale.

01 | Write friendly

Write human. People want to read something that they can relate to but also has an approachable tone. It’s easy to get caught up in sounding like a salesperson who’s only mission is to sell.

02 | Make your message relevant.

Nearly 60% of email users will mark a message as spam if they receive too many or irrelevant emails from the same sender. Why are you writing the email, and how can it add value to your customer’s life?

03 | Aim to engage first

What should an engaging first email include?

  • Communicate a promise of value
  • Once opened, the email should benefit the subscriber or customer
  • Build trust

What is the opposite of an engaging email? An unread one. Or worse, an unopened one.

You can’t escape the facts. Emails that don’t capture their prospects’ attention within the first few seconds didn’t do enough.

04 | Create some urgency

Creating urgency is an undeniable way to compel action. Psychologically, we as humans hate missing out. We want the best deals, and we want them now.

Urgency can be a marketer and a salesperson’s greatest weapon if used wisely. Having a short window of time encourages the customer to take action without overthinking the purchase.

We are inherent procrastinators and will always choose to put things off, like grabbing our credit card and making a purchase. Creating urgency makes procrastinating much harder because if you wait around too long, the deal won’t be there when you come back a week later.

Urgency should be authentic, possess creativity, and should add value to your customer’s life.

This tactic of creating urgency can quickly be overused, so be careful only to use it when the email genuinely calls for immediate action.

05 | Evoke curiosity

Subject lines that create gaps of missing information urge more clicks. Why? It’s human nature to fill the gaps of the unknown by reading what’s inside. Even with a catchy opener, making sure that there is still closure at the end of the email will keep customers from feeling betrayed after opening.

06 | Get personal

Pack an emotional punch with the email headlines. Personalization, including adding the subscriber’s name to the subject line, shows that the brand cared enough to get it right. According to Optin Monster, addressing customers by their first names in the subject line can boost open rates by 10–14%.

If you want 15 minutes of a customer’s time, you have to give them 5 of yours first by researching who they are.

07 | Use emotion

UNICEF’s powerful subject line reads: Will you put down your phone to save a child’s life?

This subject line is both powerful and relevant. Individuals who are always on the go tend to open emails using their mobile phones. A subject line like this would make anyone stop and consider the looming question.

08 | Tell them what’s inside.

Sometimes simplicity is the best move. Transparency in a subject line upfront can build trust.

My Turn

I decided to test my cold-email skills by scripting a personalized email sequence for the growing startup, Fast.

Fast is a 1-click, password-free checkout experience that cuts down minutes into seconds. It really is that fast.

I decided to target two companies I could easily see benefited by faster checkout technology — Brooklinen, a high-end luxury sheet company, and Love Wellness, a women-led personal care and supplement company.

Initial Cold Email for Brooklinen:

Subject Line: There’s fast, and there’s faster

Recipient: Julia Babina | SVP, Operations & Customer Experience at Brooklinen

Contact Information: julia@brooklinen.com | Verified on Hunter.io

Hi Julia!

As the SVP of Brooklinen, customer experience is your second language. Improving customer interaction on all levels is where your expertise lies and why I fully believe you’re the best person to contact about bringing on board a faster checkout experience for Brooklinen customers.

Since Brooklinen is growing fast, I’m sure it’s safe to say we both want your customers to be able to check out with a cart full of luxury sheets even quicker.

Now that’s two luxuries for the customer: Sateen sheets and the fastest, most secure checkout they’ve ever seen.

Here at Fast, we don’t compromise quality for quantity, and neither does Brooklinen. Our 1-click checkout takes the hassle out of yours.

No more having customers create an account only to fill out a tedious form of personal information they’ve likely filled out a dozen times in the past week.

Together, we can skip the line(s) and get straight to the good parts. High-quality sleep for your guests. Heightened sales for Brooklinen.

Let’s set up a time to talk about what Fast can do for Brooklinen. Are you available for a call on the 8th?

And of course, I’ll get back to you fast.

Madison @ Fast

Follow-up Email for Brooklinen:

Subject Line: Re: There’s fast, and there’s faster

Julia,

Fast can help you cut out all the hassle that comes with online checkout.

Let’s give your customers another reason to shop at Brooklinen.

Are you open to learning more?

Madison @ Fast

Initial Cold Email for Love Wellness:

Subject Line: Fast can improve LW’s checkout experience

Recipient: Amanda Kwasniewicz | VP, Customer Experience & Journey at Love Wellness

Contact Info: amanda@lovewellness.com | Verified on Hunter.io

Hi Amanda!

This time last year, Lauren Bosworth said in her one-on-one with Forbes that Love Wellness had “no plans to slow down anytime soon.”

Here at Fast, we love the fast-lane, and from the looks of it, so does Love Wellness.

The checkout process can cause all kinds of headaches for customers — long forms and forgotten passwords, to name a few.

Love Wellness is all about helping customers to live a fuller, cleaner life. And for LW customers, that starts at checkout.

Let us clean up the checkout process for your guests and bring in our secure 1-click, password-free technology.

Lauren said it first. There’s no slowing down.

Would you be open to learning more?

Madison @ Fast

Follow-up Email for Love Wellness:

Subject line: Re: Fast can improve LW’s checkout experience

Hi Amanda!

I wanted to get back in touch to see if you would consider streamlining Love Wellness’s checkout process with Fast.

Love Wellness is changing the way women view their health. With the help of Fast technology, we can help make that a reality for your customers in a matter of seconds.

Let’s set up a time to talk about what Fast can do for Love Wellness. Are you available for a call on the 8th?

Madison @ Fast

Although it takes more effort upfront, I decided to personalize these first-contact emails with Brooklinen and Love Wellness. If we can make first impressions in just 7 seconds, how long will it take a prospect to decide that my email isn’t worth reading (or opening)? I imagine it’s less than that. Personalization upfront makes an impact (and ultimately leads to a closed deal!)

Prospect Personalization

Personalization with these emails is vital. Combing through a prospect’s Linkedin, Twitter, or any other form of social media to gain a deeper perspective of how you can connect with them will help any outreach go the second mile.

According to Flip the Script, SDRs can use five buckets to personalize a cold-email. I will cover the first four with this post.

01 | Self-Authored Content

Any piece of content that is created by the prospect is fair game. Webinars, Articles, and Posts are all opportunities to show that you put in the research to have a proper understanding of the person you’re contacting.

02 | Engaged Content

Anything that your prospect shares, likes, or comments on will fall into this second bucket. It’s not nearly as personalized as self-authored content, but it’s still useful if a prospect isn’t as active in the content creation arena.

03 | Self Identified Traits

A prospect’s Linkedin headline, profile line, and company line are great places to obtain some customization to add to a cold email. When it’s clear that your prospect isn’t heavily engaging with other content on social media platforms, it’s acceptable to use self-composed profile pieces to warm up an initial email.

04 | Junk Drawer

The junk drawer bucket consists of a compilation of random facts such as where the prospect attended school, recommendations they’ve received, or hobbies they regularly enjoy. Playing around with these personalization pieces can be risky if not directly tied to the email’s purpose. Don’t include that you know your prospect went to Yale if it has nothing to do with why you’re composing the email.

The Pillars of Attractive Emailing

01 | Prospect Centric

Talking about what your company does, no matter how impressive it may be, isn’t as appealing as discussing what your company can do for the prospect. Relating everything to the customer will ensure that they feel considered.

02 | Pain Centric

Outreach emails should address how the product or service alleviates pain for the customer, not what pleasure it adds.

03 | Fluidity

The premise (personalization), the body of the email, and CTA should all be connected.

04 | Relevance

When a prospect opens a cold email, they look for one thing. What’s in it for them? They aren’t as concerned with how a company does something, but rather what a company can do for them. It’s crucial to make these first emails relevant, or customers will assume it’s an automated email.

05 | Brevity

Be concise. Never use more words than you have to.

06 | Nocetiablity

High open-rates without clickbait is the ultimate goal.

7 Deadly Sins of Messaging

According to Flip the Script, seven mistakes should be avoided at all costs when cold-emailing. Being unaware to avoid these principles can cost you the whole deal.

01 | Being too casual or silly

02 | Wasting text

03 | Establishing authority over the prospect

04 | Questioning the prospect’s authority

05 | Leading your prospect to feel a certain way

06 | Glorifying yourself (or the company’s accomplishments) over the prospect

07 | Making the prospect feel stupid

Cold-emailing takes time to master, and there is always another aspect of the craft to learn. I am on a journey to make that learning a mission.

Key Takeaways

  • Personalization, Personalization, Personalization.
  • Putting in the effort to research the prospect upfront will establish a better relationship and encourage trust through the pipeline.
  • Cold-emailing is customer-focused, not company-based.

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Madison Gary

I’m fascinated by words and captivated by the power they can have in everyday communication. My story is still unwritten and the pen is in my hand.